Carry on Wayward Winchester
by otkcp
Summary: Somethings up with the universe and well now Dean is left raising five different versions of his daughter Emma (all now separate people). Twisted from canon a lot. Spanking in future chapters. Please read and review...flames will be ignored.
1. The Emma Dilemma Part 1

A/N: Just so you know I am from New Zealand and have never been to the USA, so I used google to find a town. I know nothing about said town so I'll be mostly describing fictional places (motel, diner, department store etc) Anyone who lives in or has been to this place I'm sorry if I say anything wrong, no offence meant.

Warnings: This twists canon beyond belief so if you have a strictly canon heart, you prolly shouldn't read this fic. There will be spankings and other forms of old school discipline in this fic which I don't agree with in terms of non-fictional children in non-fictional settings. But this is a work of fiction so please remember that. There is likely to be slash pairings in later parts as well us mentions of polyamory and open relationships (I'll warn in those parts if needed) as well as swearing, violence and possible sexual instances. There will also be a lot of fluff and family cuteness. Spoilers for some parts of canon from seasons 1-8 most likely.

Disclaimer: My name isn't Kripke and none of this belongs to me, I just like to mess with canon =)

**Carry on Wayward Winchester**

**The Emma Dilemma **

**Part One**

**July 2012**

**Topeka, Illinois **

**Alden Family Motel and Camp Grounds**

**Room 11**

The Winchester boys had settled into yet another dingy old motel room, the walls were a horrid salmon pink, the carpet was a stained and worn cream colour. Against the main wall stood two queen sized beds with an awful floral pattern bedding that matched the closed curtains. Dean made himself comfortable on one of the beds and had kicked off his well worn boots, a slight stench of sweaty socks and old shoes made its way to Sam's nostrils. Wrinkling his nose at the offending smell the taller brother looked around The rest of the room, it was a good size, it had a small run down but functional bathroom to the right of the main door as you came into the room.

"Dude, your feet reek!" Sam griped at his older brother who shrugged his shoulders, smiled at Sam and wriggled his stinky toes around.

"Don't be such a bitch, Sammy" Dean replied, smiled still on his face.

Sam just rolled his eyes at his brother's antics, grabbed the six pack they had brought with them and popped it into the old mini-fridge with a broken light that was built into the small kitchenet. Once the beer was put away and cooling the hunter sat himself at the rickety old dining table that stood opposite the beds and pulled out his laptop to start on his research.

A television, closet and a locked door that led into the adjoining room next door completed the room. It wasn't much, but it was semi clean, affordable and enough out of the way that no one would notice them. It was nothing they weren't used to by now, that was for sure. From what the brothers had seen, the rest of the motel complex was nice enough, it had it's own laundry mat that was accessible to the guests. The outside grounds had an outdoor pool and spa that was fenced off. Their was a nice barbecue and picnic area for families and even an old wooden jungle-gym for kids who passed through. It even had it's own little Mom 'n' Pop, twenty-four hour diner on grounds. It was a nice place, better then some they'd stayed at in the past, these boys had grown up in places like this.

The pair of brothers had been apart for the past week and a bit, Dean had taken some time off to go visit Lisa and Ben. Something he had been doing much more of since Lisa had finally come clean with him about his position as one Benjamin Isaac Braeden's biological father. Both father and son had been very happy with this news, Dean had been a little pissed and a little more then hurt by Lisa's lie but he had moved past it, he was Ben's Dad and well that meant something to Dean. Ben had been pissed at first too but now, nearing the two year mark since finding out, the three of them had fallen into a nice pattern of being a family of some kind. Dean wasn't the only one with a teenage son that he was trying to be there for while balancing the whole hunting gig.

Sam had met his son Jacob a little over a year ago now. The kid's Mom was a Kitsune that Sammy had met and not long after, lost his virginity with when he was barely older then his kid was now. Amy had called him after falling sick, she had told him about Jacob, had explained that the boy was his and had lucked out genetically because he had been born human. Things had started off slowly with Sam and Jacob just getting to know each other during the seven months that it took for the disease to claim Amy's life. Now it was five months since Jacob had lost his Mom. The father and son duo had adjusted pretty well, of course the kid missed his mother, but he loved his Dad, Uncle Dean and Uncle Bobby. Not to mention he and Ben were only months apart in age and had fallen easily into a pattern of being cousins.

Sam and Jacob had been staying with Bobby this time while Dean visited his son. Sam had left the kid with the grouchy old hunter while he went to meet his brother for a hunt half way between Battle Creek, Michigan and Bobby's place in South Dakota. Which of course meant that Sam had his own car with him this time, his shiny black Dodge Charger STR 8, not something he did often, he and Jacob usually rode in the Impala with Dean. Although Sam wasn't as attached to his car as Dean was with his 'Baby', but he did prefer that his son ride in it, what with the seat belts and all. As he settled in to research, Sam figured he should flick his son a quick text, just to let him know that both his Dad and Uncle had made it to their destination safe, sound and in one piece.

'Hey Jake, made it to Illinois with no problems. I'm with your Uncle now and he's being his usual charming self. Be good for Bobby and have fun. I should be back in a few days, maybe a week tops. Love you Kiddo, I'll call you tomorrow.' Sam sent the message off, looking back at his computer screen as he waits for the familiar sound of his phone letting him know his son had replied.

It didn't take long for the familiar jingle to sound from the little silver cellphone. 'Cool Dad, glade you got there. Uncle Dean is awesome like that. Uncle Bobby is making me some grilled cheese right now. Have a good hunt and stay safe, love ya too and say hi to Uncle Dean from me too'. Sam smiled as he read his son's reply, he really did love that kid.

"Jake says 'Hi'" He tells his brother, motioning toward his phone.

"Of course he does, kid loves me" Dean said with a smirk, he loved being an Uncle and Jacob was a lot like Sammy had been when he was younger, but without as much of the angst and attitude.

"Yeah, so how are Ben and Lisa doing?" Sam asked, he couldn't deny the truth, Jacob did love his Uncle.

"They're good, Lis is as hot as ever and well Ben is all teen boy now" Dean had a big smile on his face as he thinks about his now teenage son. At thirteen Ben is so much like Dean had been, minus the weapons, training and hunting. Ben had the attitude, the swagger and that smirk that draws the girls right on in.

Sam could tell from his brother's smile that Ben was probably a ladies man just like his Dad had been. The brothers talked for about their sons for a bit, telling each other what had happened with the boys over the week they'd been apart. As they talked, Sam continued on with his research but really it wasn't likely to be much more then a simple salt and burn. But a job was a job so they still needed to learn as much as they could before they head out, their father's training still ingrained deep in them. They soon fell into a comfortable silence as Sammy researched and Dean cleaned the guns. The silence was soon interrupted by a few sharp raps on the motel door.

Sam sighed and pulled himself up from his chair and made his way to the door, whoever was on the other side was still knocking, only the knocks were more frantic, as if the person doing the knocking was getting more and more desperate. Pulling the door open Sam was surprised and a little confused by the sight he was met with. Standing in front of him was five blond hair girls. The eldest was a teenager about fifteen or sixteen, she was holding a tiny baby who was still new enough that she was still pink faced. Next to the teen was another girl, no more then ten or eleven, on her his sat another baby but this one was over the year mark but not quite nearing two years yet. Standing just in front of the two girls holding babies was a bitty wee thing who must have been about five.

It was the teen that really caught Sam's eye, the girls blond hair and green eyes were familiar "Emma?" Sam asked aloud, still shocked and more then a little confused.


	2. The Emma Dilemma Part 2

**Carry on Wayward Winchester  
The Emma Dilemma**

**Part Two**

**July 2012  
Topeka, Illinois  
Alden Family Motel and Camp Grounds  
Room 11 **

Sam was still standing at the door, looking confused. Dean had jumped up from his spot and joined his brother at the door, with his own shocked look on his face. Sure enough, standing at the door was his daughter, his supposidly dead, not human daughter. Only it was just the sweet sixteen year old this time, he only recognised the one year old, the little one who was about five and the sixteen year old, all of them were Emma and that was confusing as all hell. Dean looks from Sam to the five girls and back again.

"Dude, is this real?" he asks, although he isn't sure he's really looking for an answer or not.

Sam reaches over and pinches him firmly on the left arm "yup, it's real" he confrimed with a smirk.

"Ouch Sammy, what did ya do that for?" Dean whined as he glared at his younger brother and retaliating with a sharp cuff upside the head. Causing the one year old to laugh at the silliness between the pair of brothers.

"Answering your question" Sam said, bitchiness starting to seep into his voice now.

"You coulda done that without pinching me bitch!" the older brother said with a huff.

The teenage girl cleared her voice, regaining the attention of the bickering brothers "can we move this inside, I want to put the baby down" she asked, it was polite enough but there was a clear hit of attitude behind those words.

The brothers nodded to each other and moved aside to let the girls past and into the room. The eldest sauntered in, walked straight over to the nearest bed and carefully placed the new born baby into the centre of the bed, grabbed the pillows and put one on either side, just incase. The next eldest of the girls also unloaded her own arms, placing the toddler on her little feet. Giggling, the toddler shook her little hips and stretched a little, clearly happy to have been put down. A little head of blonde hair bounced as the little girl pulled herself onto the empty bed, turning to look at Sam and Dean curiously.

"So, uh what the hell?" Dean finally asked as he stared at the girls, still trying to figure it all out.

The blonde teen turned to him and frowned "I don't really know, we just kind of turned up on the side of the road together" she started to explain.

"I knew we were all the same but different now too, I don't really know what happened" she concluded with a shrug.

Trying to process all of the information Sam asked a question next "How did you know where to find us?".

"We were just down the road, we started walking this way and I guess I recognised the car even though you weren't driving it last time, I just kind of knew" the teen explained.

The boys figured they needed to do some tests, bringing out the silver and holey water, they made quick work of confirming that the girls were now in fact all human. After the tests were done, Dean offered up a quick prayer to Castiel, hoping he would be able to get some answers from the celestial being. Cas was too busy doing whatever it was that the angel did when he wasn't helping the Winchester brothers, but he did answer the prayer with a quick phone call to offer what little he knew about the situation. The angel confirmed what they knew, the girls were human and that he believed they were likely to be individuals with their own destinies.

'Well son of a bitch' Dean thought to himself, realising that he was now a Dad with five daughters. He had only really just gotten use to being Ben's Dad and now he had five little blonde girls to take care of. They would need things, clothes, toys and baby stuff like bottles, formula and well damn the little two would need diapers too. As if reading his big brother's mind, Sam spoke up.

"We're going to have to hit the shops" he said "the girls are going to need supplies".

Dean nodded "yeah, okay so Emma you up for a shopping trip?" he asked, not really sure which of the girls he was really asking, seeing as all of them were technically called Emma.

"You know, we can't all keep the name Emma if we're here for real" the teen said, seeming to be on the same train of thought as Dean.

The hunter nodded and said "well what do ya want to do about it?" he asked her.

"I don't want to keep being Emma, and I'm sure as hell not letting you or anyone else pick my new name" she said, her voice filled with attitude and a determained look in place on her pretty face.

The next eldest spoke up next, with just as much attitude and determination in her own voice "well I'm keeping Emma, its my name and I don't wanna change it".

"Fine with me, so you're are Emma then, and you can be whatever the hell you want to name yourself" Dean said, because really he didn't want to have to name them anyway, although he figured he'd have to name at least the babies, but that could wait for now.

"Then who will I be if I'm not Emma now?" the five year old asked from her spot on the bed, her head cocked to the side and a curious look on her face.

"What about Hannah?" Dean asked "like Hannah Montana?" he continued, remembering his reference to Hannah Montana he had made about the girl the first time he had seen her. The little one looked confused for a moment.

"Whose that?" she asked innocently.

Sam smiled at Dean, typing a quick search into his laptop and playing a clip of Hannah Montana singing for the littler girl to see. Her face lit up as she listened and nooded her head enthusiastically before saying "yeah, I wanna be Hannah!".

"Right, well seeing as you two have names now, we should probably getting you some stuff too" Sam suggested.

Dean scooped up the tiny baby girl from the bed, he was surprised how light she was and how nice she felt in his arms. He gestured to the toddler and looked pointedly at Sam, who got the suggestion and picked the little girl up, placing her onto his right hip. As they made their way out the front door, Dean was surprised to feel the newly named Hannah, slipping her little hand into his bigger one and walking beside him with a skip in her step as they crossed the busy road to the closest department store .

…...

Dean stood in the baby aisle, trying to figure out what size diapers he would need for his two newly required baby daughters. The smaller of the two was sleeping peacefully in his cart, while the older one was in Sam's cart. Sam was currently looking at electronic gadgets he believe that the kids would need to keep them entertained on the road. Picking up a package of diapers that said they were for newborns, Dean tossed it into the cart. He grabbed another couple of packages that he figured would fit the toddler and moved onto bottles. He picked up two six packs of baby bottles, one pack was taller and thiner bottles, clear coloured, three with pink lids and three with purple. The other pack were short and round bottle, clear as well, with white lids and caps. He checked to make sure that he had the right teets for each of the babies, a vague memory of his father trying to feed baby Sammy with a teet that was a size too big and the poop baby almost drowing in formula.

Next came the tins of powdered formula, one tin said for newborns on the side and the other said twelve to eighteen months, he figured that that would do them for now. He grabbed some pacifiers for both babies too, figuring it'd be a helpful habbit while on long rides with the babies. Wipes, rash cream, baby powder and teething gel were added too, as were several colourful jars of baby food for the one year old.

"Aw ain't she just a little cutie" a middle aged woman said as she spotted the sleeping baby in the cart "she's just a new one, what's her name?" she went on to ask.

Dean blurted out the first name that came to mind in reply to the lady's question "Chevy". The lady smiled and cooed at the baby for a little bit, she was still doing this as Sam came into the aisle with the blonde one year old babbling away from her seat in his cart.

"Oh aren't you a little cutie too?" she said as she turned to the toddler "what's your name then little one?" she asked with a sickly sweet tone.

"Uma" the little girl said clearly, Dean figured she was trying to say Emma, but the name that popped to the front of his thoughts at that was "she's Zuma" he told the woman, wondering if he had really just named his youngests Chevy and Zuma, but thinking he quite liked it either way, Zuma Winchester had a kind of ring to it really.

After the woman had finally moved on, Sam turned to Dean and said "Zuma, really?" Dean just shrugged and mumbled something incoherint under his breath.

"Where are the kids?" Dean asked as he noticed that none of the older three girls were anywhere to be seen.

"The teenager is picking out and trying on some clothes, Hannah and Emma are picking out a few toys in the next aisle over" Sam said without hesitation.

"Right, well we should grab some clothes for the rest of them and get this show on the road" he said as he pushed the cart off towards the baby clothes section at the end of the aisle.

…...

After nearly three hours of shopping the older girls each had a duffle bag fulled with clothes, toiletries and a backpack with some toys, books and other fun things. The eldest who had finally announced her name as Cobalt (after the bar her parents met at) had a matching duffle and backpack, both were a dark purple and black checkard pattern. Emma's bags were both a pale purple colour, while Hannah's were pink. The newly named Zuma and Chevy had a shared light blue duffle and a black diaper-bag.

They had gone back to the motel room, paid extra to have the adjoining room opened up. Dean had also requested a couple of cribs for the babies, but they only had one to spare. Chevy was swaddled and sleeping peacefully in said crib, while Zuma was sleeping on Dean's bed, right next to him as he watched some old monster movie on the television. Sam was on his laptop again, he had called Bobby to tell him something had come up and they needed someone to cover for them on this hunt. He had assured him that no one was hurt and that all would be explained when they arrived sometime the next night.

The older three girls were in the next room, watching their own television and playing with some of their new toys and gadgets. It was calm and almost peaceful. Dean had even survied both girls diaper changes and bottles without too much drama. Sam had gone and picked up some food for dinner and all seemed to be going pretty well. But Dean knew it wouldn't last, he could remember what he and Sammy had been like as kids, the trouble they caused and the times they'd spent nursing sore butts. Plus he'd been Ben's dad for a while now and well Jacob had been around for a bit now too. All kids brought chaos, but Winchester kids? That was a whole nother type of chaos and Dean wondered if he was ready for it at all?

Well it was going to happen, whether he was ready or not and well he would just have to deal.

…...

Castiel felt bad, he should have told Dean what he was so busy with but he knew the hunter would find out soon enough anyway. The angel was standing in a motel room off of some main road that lead into a small town somewhere in North Dakota. There was an unconsious man laying on each of the two beds in the room. One of the men was considerably older, somewhere in his late fourties or maybe his fifties but still looking good for his age. He had a head of dark hair and face with matching scruff.

The younger man on the other bed was smaller and leaner, although neither man was at all fat. In fact the older man seemed to be all muscul. The younger couldn't be much older then twenty, difinatly this side of the quarter century mark. His hair was not all that short but by no means long either, it was a dirty blonde colour. Although the similarities were very subtle, they were there. The two men shared half the same DNA after all, seeing as they were father and son.

Noticing that John was stirring, Castiel decided it was time to leave. His job was done, John Winchester had been returned to earth from Heaven, very much alive and the same was to be said for his son Adam, who had been pulled up from Hell and would get his second chance with both his father and his brothers.

John woke with a gasp, it took him a few moments to get his bearings before he turned and noticed he wasn't alone. Walking over to the other bed caustiously he noted that it was his son Adam.

"Adam, son, wake up" he spoke almost frantically as she shook the boy's shoulder and tried to rouse him.

As the blonde opened his eyes and spotted his father he asked "Dad? What's going on? Where am I?".

These were of course all good questions, but not ones John had any answers to right now.

**A/N: I know it's not the longest part (although longer then the last) but I just wanted to give the back story and set everything up for the others I have planned. Hope you enjoyed and let me know what you think and what you would like to see next.**


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